Purdue University Purdue e-Pubs Open Access Dissertations Theses and Dissertations Fall 2013 The heC mistry of Flavonoids in Model Beverages and Human Milk Brian Jay Song Purdue University Follow this and additional works at: https://docs.lib.purdue.edu/open_access_dissertations Part of the Food Science Commons Recommended Citation Song, Brian Jay, "The heC mistry of Flavonoids in Model Beverages and Human Milk" (2013). Open Access Dissertations. 64. https://docs.lib.purdue.edu/open_access_dissertations/64 This document has been made available through Purdue e-Pubs, a service of the Purdue University Libraries. Please contact [email protected] for additional information. Graduate School ETD Form 9 (Revised 12/07) PURDUE UNIVERSITY GRADUATE SCHOOL Thesis/Dissertation Acceptance This is to certify that the thesis/dissertation prepared By Brian J. Song Entitled The Chemistry of Flavonoids in Model Beverages and Human Milk Doctor of Philosophy For the degree of Is approved by the final examining committee: Mario Ferruzzi Chair John Burgess Christian Butzke Fernanda San Martin-Gonzalez To the best of my knowledge and as understood by the student in the Research Integrity and Copyright Disclaimer (Graduate School Form 20), this thesis/dissertation adheres to the provisions of Purdue University’s “Policy on Integrity in Research” and the use of copyrighted material. Approved by Major Professor(s): ____________________________________Mario Ferruzzi ____________________________________ Approved by: Brian Farkas 08/21/2013 Head of the Graduate Program Date i THE CHEMISTRY OF FLAVONOIDS IN MODEL BEVERAGES AND HUMAN MILK A Dissertation Submitted to the Faculty of Purdue University by Brian Jay Song In Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy i December 2013 Purdue University West Lafayette, Indiana ii To my parents, Ki Hwan and Hyon Sik Song, who made my growth and prosperity possible. ii iii ACKNOWLEDGEMENTS I would like to express my deepest gratitude to my family who have fully supported all my efforts. I would like to thank my major professor, Dr. Mario Ferruzzi, for being a great advisor and always pushing me towards my highest potential. Your encouragement, attitude, and research prowess have been a great influence during my graduate studies and will continue to influence me in the future. I would like to thank my academic committee members, Dr. Jay Burgess, Dr. Christian Butzke, and Dr. Fernanda San Martin. Your insight through my studies have allowed me to become a superior scientist. I would like to thank my fellow lab members, Andrew Neilson, Shellen Goltz, Nicolas Bordenave, Tristan Lipkie, Sydney Moser, and Tzu-Ying Chen, for their aid and support iii throughout my graduate studies. Our combined efforts allowed us to surpass many obstacles and simultaneously created wonderful memories that I will never forget. iv I would like to acknowledge the undergraduate research assistants, Claire Burtch, Stacey Hirt, Christopher Manganais, and Laura Willis, for aiding in the experiments discussed within this dissertation. Finally, I would like to thank Mrs. Patricia Grantuskas, Mrs. Laura Lepore, and Dr. Mary Ann Lovelace for encouraging my academic growth and indulging my scientific interest throughout my youth iv v TABLE OF CONTENTS Page LIST OF TABLES ............................................................................................................. ix LIST OF FIGURES ............................................................................................................ x LIST OF ABBREVIATIONS ........................................................................................... xii ABSTRACT ............................................................................................................... xiv CHAPTER 1. REVIEW OF LITERATURE .................................................................. 1 1.1 Introduction ............................................................................................... 1 1.2 Flavonoid Molecular Structures ................................................................ 1 1.2.1 Flavan-3-ol Molecular Structure ......................................................... 2 1.2.2 Anthocyanidin and Anthocyanin Molecular Structure ........................ 3 1.2.3 Flavonol and Flavanone Molecular Structures .................................... 5 1.3 Biosynthesis of Flavonoids ....................................................................... 6 1.4 Common Dietary Sources of Flavonoids .................................................. 8 1.4.1 Flavan-3-ols ......................................................................................... 9 1.4.2 Anthocyanins ..................................................................................... 11 1.4.3 Flavonols ........................................................................................... 13 1.4.4 Flavanones ......................................................................................... 14 1.5 Flavonoids and Health ............................................................................. 14 1.5.1 Oxidative Stress ................................................................................. 14 1.5.2 Inflammatory Stress .......................................................................... 15 1.5.3 Cardiovascular Disease ..................................................................... 16 1.5.4 Cancer ................................................................................................ 17 1.5.5 Neurodegenerative Diseases .............................................................. 17 1.6 Flavonoid Absorption, Metabolism, and Bioavailability ........................ 18 1.6.1 Flavonoid Absorption ........................................................................ 19 v 1.6.2 Flavonoid Metabolism ....................................................................... 22 1.6.3 Flavonoid Bioavailability .................................................................. 23 1.6.4 Flavonoid Tissue Distribution ........................................................... 24 1.7 Flavonoid Stability .................................................................................. 25 1.7.1 Oxygen and Oxidation ....................................................................... 26 1.7.2 pH Stability ........................................................................................ 29 1.7.3 Temperature ....................................................................................... 31 1.7.4 Light .................................................................................................. 33 1.8 Interactions with Protein ......................................................................... 34 1.9 Research Aims ......................................................................................... 35 vi Page CHAPTER 2. PHOTO AND THERMAL DEGRADATION OF ANTHOCYANINS FROM GRAPE AND PURPLE SWEET POTATOIN MODEL BEVERAGE SYSTEMS ....................................................................... 39 2.1 Introduction ............................................................................................. 39 2.2 Materials and Methods ............................................................................ 41 2.2.1 Materials ............................................................................................ 41 2.2.2 Model Beverages ............................................................................... 42 2.2.3 Photo and Thermal Stresses .............................................................. 42 2.2.4 Anthocyanin Analysis ....................................................................... 43 2.2.5 Kinetic Models .................................................................................. 45 2.2.6 Experimental Design and Statistical Analysis ................................... 45 2.3 Results and Discussion ............................................................................ 46 2.3.1 Anthocyanin Profiles ......................................................................... 46 2.3.2 Impact of Thermal Stress on Grape Anthocyanin Degradation Rates .. .......................................................................................................... 47 2.3.3 Impact of Model Beverages on Anthocyanin Degradation Rates Through Thermal Stress .................................................................... 50 2.3.4 Arrhenius Behavior and Activation Energies .................................... 52 2.3.5 Grape and Purple Sweet Potato Anthocyanins Under Thermal Stress .. .......................................................................................................... 54 2.3.6 Impact of Model Beverages on Anthocyanin Degradation Rates Through Photo Stress ........................................................................ 56 2.3.7 Grape and Purple Sweet Potato Anthocyanins Under Photo Stress .. 58 2.3.8 Conclusions ....................................................................................... 62 CHAPTER 3. ASSESSMENT OF PHYTOCHEMICAL CONTENT IN HUMAN MILK DURING DIFFERENT STAGES OF LACTATION ................ 63 3.1 Introduction ............................................................................................. 63 3.2 Material and Methods .............................................................................. 66 vi 3.2.1 Chemicals and Standards ................................................................... 66 3.2.2 Human